Naphthenic alcohol esters of fatty acids



Patented Aug. 6, 1935 NlTE ST NAPHTHENIC ALCOHOL ESTERS F FATTY ACIDSAlfred Kirstahler, Dusseldorf, and Wilhelm Jacob Kaiser,Dusseldorf-Benrath, Germany,

signors to firm Henkel & (Die. Gesellsohaft mit beschrankter Haftung,Dusseldorf, Germany No Drawing. Application December 23, 1932, InGermany January 4,

Serial No. 648,725. 1932 2 Claims.

unsubstituted or substituted, saturated or unsaturated, aliphatic,hydroaromatic or aliphaticaromatic compounds containing hydroxyl, andhaving at least 6 carbon atoms, and on the other, of acids containingreactive halogen atoms or the derivatives or substitution products ofsuch acids.

The said valuable high-molecular compounds are obtained according to theinvention by converting the said esters with organic hydroxy compounds,aliphatic, hydroaromatic or aliphaticaromatic alcohols and phenols. Theorganic hydroxy compounds are preferably employed in the form of theiralkali compounds.

Of the hydroxyl compounds which are necessary for the synthesis of thesaid esters, the aliphatic alcohols containing 6 or more carbon atomsand having a saturated or unsaturated nature, also the naphthenicalcohols and the resin alcohols have been found to be particularlysuitable. The alcoholsobtainable from paraffin, also aliphatic-aromaticalcohols, such as benzyl alcohol, beta-phenyl-ethyl alcohol and the likemay be employed, likewise polyvalent alcohols. It is also possible,however, to employ other aliphatic compounds containing hydroxyl groups,and having at least 6 carbon atoms, such as for example the saturated orunsaturated hydroxy fatty acids and their derivatives, such as estersand amines, and the hydroxyalkyl esters of fatty acids and the like, thehydroxyalkyl ethers or hydroxyalkyl thioethers of the higher alcoholsand so on.

Of the acids which contain reactive halogen atoms and which arenecessary for the synthesis of the said esters, the lat-halogen fattyacids, such as mono-chloracetic acid, monobromsuccinic acid,dichlor-acetic acid, a-bromolauric acid have been found to beparticularly suitable. Instead of such (ii-halogen acids, however, it isalso possible to employ aliphatic carboxylic acids which are substitutedby halogen in other positions, furthermore carboxylic acids of otherseries containing replaceable halogen atoms, such as for example benzylchloride-4-carboxylic acid, 2- chlorobenzoic acid or its substitutionproducts, such as for example 5-sulpho-2-chlorobenzoic acid.

The new high-molecular compounds, in so far as they are insoluble inwater, should find an appllcation in the perfume industry, furthermoreas softening agents or the like.

The water-soluble products manufactured according to the presentinvention possess saponaceous properties.

They may be employed alone or together with other soaps, saponaccoussubstances, filling substances, compounds which give off active oxygenand the like.

Examples (1) 23 parts by weight of sodium metal are dissolved in 600parts by weight of phenol, and 262 parts by weight of dodecylchloracetic. ester are added to this solution. The mixture is thenheated for 8 hours at 100 C. in the absence of atmospheric moisture.

After working up in the usual manner, the dodecyl phenoxyacetic ester isobtained as a white crystalline mass.

Meltin point 33-34" C. Boiling point 240-245 C. at 17 The tetradecyl andhexadecyl esters of phenoxy-acetic acid, and their mixtures, may bemanufactured in a similar manner.

The same com- We claim:

1. Anew class of hydroaromatic esters of carboxylic acids correspondingto the formula R O-R -CO-O-R in which R denotes a radical of a groupconsisting of fatty acid acyl radicals and aryl radicals, R CO-O denotesa saturated fatty acid radical and R denotes a radical of naphthenicalcohol.

2. A new class of hydroaromatic esters of carboxylic acids correspondingto the formula R O-R CO-O-R in which R denotes an aryl radical, R -CO-Odenotes a saturated fatty acid radical, and R denotes a radical ofnaphthenic alcohol.

ALFRED KIRSTAHLER. WILHELM JACOB KAISER.

